Sam and Annie Cobb first homesteaded 160 acres on Anna Maria Island in 1896 in the area now called Holmes Beach. John R. Jones and Jose Casanas soon joined the Cobbs. Jones piloted boats running between Tampa and Cuba. Casanas relocated from the Canary Islands in search of mullet fishing grounds.

The first island post office was established in 1902 in the home of the Cobbs.

The city derives its name from Jack Holmes, a developer who arrived on the island after World War II and created a 600-acre community. When the city was incorporated in 1950, Halsey T. Tichenor served as its first mayor.

A century’s worth of development may mask it, but early residents had to hack through dense jungle just to create a sandy washboard road. Back then, facing rattlesnakes, wildcats and panthers was a common occurrence.

In 1948, just two years before Holmes Beach was incorporated, Hollywood brought Esther Williams, Peter Lawford, Ricardo Montalban, Jimmy Durante and Cyd Charisse to community to film portions of On an Island with You.

Today, Holmes Beach remains a popular tourist destination with a wide array of vacation rentals, in addition to permanent and winter residents.